


Lawyer & Client

by AnotherHomosexualMale



Series: Rare/Weird Couples That Actually Make Sense In My Mind [2]
Category: Community (TV)
Genre: Anal Fingering, Anal Sex, Bisexual Male Character, Closeted Character, Kissing, M/M, Masturbation, Oral Sex, Rough Sex, Secret Relationship, Smut
Language: English
Status: Completed
Published: 2020-04-17
Updated: 2020-04-17
Packaged: 2021-03-01 22:47:16
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,386
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23694886
Author URL: https://archiveofourown.org/users/AnotherHomosexualMale/pseuds/AnotherHomosexualMale
Summary: Jeff Winger fucks former convict Willy from that iPads on wheels episode. Secret fucking, closeted bisexual Jeff Winger has a thing for raunchy men, and just tall men fucking overall.
Relationships: Jeff Winger/Willy Sebret Smith
Series: Rare/Weird Couples That Actually Make Sense In My Mind [2]
Series URL: https://archiveofourown.org/series/1719358
Comments: 1
Kudos: 22





	Lawyer & Client

**Author's Note:**

> Why not, I liked season six.

“Who was that?”

“The dean just wanted to ask me about some Greendale’s churro-eating contest… I told him th-.”

His words were cut off by the other man’s lips against his own, the hot tongue asking to enter his mouth.

“We shouldn’t be doing this...” Jeff moaned. His hands tightened in Willy’s short hair as the stronger man pressed him against the wall. One of Willy’s hands traveled lower to stroke the considerable bulge in his pants, and Jeff’s taller figure rutted against the teasing fingers, too driven by pleasure to be embarrassed.

Willy’s bearded mouth sought Jeff’s as he unzipped the lawyer’s pants. He smiled in the kiss as the little resistance that Jeff had posed earlier seemed to vanish.

“Dude, you’re my client…” Jeff tried reasoning futilely, even as his hands ran over Willy’s powerful chest, teasing his nipples. “ _And_ you have tried to murder me in the past…”

Willy just hummed in response and helped Jeff out of his coat. “Water under the bridge Mr. Winger...” _Shit_ , he was such a sight when he was all dressed up in that tight suit. The court should put Jeff behind bars; looking that good in a simple suit should’ve been illegal.

Willy’s own jacket and shirt were long gone. He could see Jeff’s eyes darkening as they ran over the ex-convict hairy arms. The lawyer’s hands followed his line of sight, tracing his arms lightly.

It wasn’t the first time Jeff had seen him naked, neither was it the first time that they were this intimate with each other. But every time that they touched, it was never the same. A different place, a different room, a different wall, a different car. Questions came back at Greendale: Annie thought his absences were a product of him going to some law seminar, Britta thought he was definitely fucking some girl in Fresno, and Abed just seemed to shrug every time, although Jeff knew that he knew... Yet none of the others would ever believe that Jeff Winger, Great Lawyer of Greendale’s Community College, was fucking the convict guy that failed to throw him down the stairs, and fought against him by controlling an iPad with wheels. But it was that exact guy, that random episode guy. The same hands and the same lips. The same darkened gazes.

Maybe Pierce had been somehow right all along... Jeff was pretty damn gay for a certain type of men. The men that he felt he couldn’t defeat and control. Men who used patronizing words, and had aggressive yet seductive personalities. Those men were such a huge turn-on for Jeff Winger, and just now he was finally coming to terms with this whole bisexuality mess inside of him.

Long story short, things got even harder when he decided to practice again as an actual attorney. He joined a very small law firm, and got assigned for the easy release process of a familiar face as his first task: Willy Smith, the iPad-robot murderer... Since apparently, the fact that the convict was innocent of murder after all, it was quickly enough to just fill his exit paperwork. And right after that, things escalated quickly.

It was after Jeff picked him up from jail since it was “part of his job as the newbie.” as the other lawyers had told him, Willy had convinced him to go for a drink. _“C’mon, Mr. Winger… I’m a free man now!”_ Sweaty forehead, and a big smile beneath that shiny beard… Willy seemed happy that Jeff had been the one to help him through his release.

Jeff didn’t say no, and the next day, shit got real when he woke up in a motel room bed with a naked Willy by his side, bites all over his neck and chest, a filled condom still attached to his own limp dick, and three bottles of cheap vodka on the dirty carpet. Just the first night of their dirty little secret, one of many more to come.

But here, in Willy’s bedroom, with the dimly lit lamps casting orange light over their skin, it felt somehow even more private than their other times. Jeff’s touches seemed more tender, lips more sensual and body even more alluring. The former inmate couldn’t stand it.

He dropped to his knees and took Jeff’s long erection in his hands, stroking him slowly. Even Jeff’s muffled moans sounded different; right then, his moans made something possessive take root inside Willy.

His lips enveloped Jeff in warmth and Jeff’s hands tightened in his hair, hips thrusting up. He knew Willy loved it when Jeff Winger fucked his mouth, loved it when he came down his throat. He knew the man never sucked anyone else. Never ate anyone out. He knew no one fucked him as good as Willy did.

They sight of Willy’s manly eyes, shining like flames in the faint light made Jeff bit down on his lips as his hips thrust faster, almost chocking Willy. His eyes watered and Willy steadied himself with his hands on the lawyer’s thighs, but he didn’t stop Jeff. It sounded filthy to Jeff’s ears, the sounds that his cock made very time it slid past Willy’s lips. So filthy that it almost reminded Jeff the kind of man that Willy was.

He was a dangerous guy, Jeff knew. It was for that very reason that he was hired as Willy’s lawyer. Willy was very smart, and still a raunchy man, pro-murder and care-less, and Jeff was among the lawyers who’d kept the man from being in jail for long.

The tattoos on his skin and the sly smirk on his face were all a proof that he wasn’t all nice, and still was up to no good.

But at that moment, he was a very attentive lover and honestly, Jeff’s penis had been sucked so many times by him, that he had forgotten to be ashamed of actually fucking another man.

His hips stuttered as Willy’s one rough hand fondled his hairy balls, while his tongue traced the underside of his cock. Willy’s tongue teased his penis as he sensed Jeff was near, and with just the lightest graze of his teeth on Jeff’s cock, Winger was groaning. He held Willy’s head in place as he came and Willy diligently swallowed all of Jeff’s cum, cleaning up his lips with a satisfied dazed smile.

Oh, but Jeff knew they were far from done. He knew it even before Willy hoisted him up and he wrapped his legs around Willy’s waist. Moments later Willy’s teeth were marking his skin as he laid on the bed. His legs spread, inviting Willy in.

Jeff tried pulling Willy up for a kiss, but the latter held his hands above his head and growled lightly.

“I almost want to keep you like this.” Willy said, tracing his lips down Jeff’s chest, biting his nipples and making Jeff hiss. “Want to just lay down beside you and tie you to myself.”

It was bold and completely unsurprising, when Jeff asked with his usual mockery, “What’s stopping you, then?”

Willy paused; his tongue dipped down to circle Jeff’s flushed nipple. “It’s just that you’re so fucking handsome, lawyer man…”

“You’re hot enough.” Jeff argued, gesturing to the other man’s body.

“Sounds like you want me to keep your ass, Winger.” Willy smirked. “Thought you didn’t like bad guys.”

Jeff smirked, “You could leave this all, you know, Willy? Join Greendale for real, get a degree, start a business... Shit, even work there as a professor like you wanted last time...”

Willy chuckled. “You’re so fucking funny, Winger. I won’t be able to afford you as my private lawyer by working as a janitor or a teacher in that school... I like you in my old ass sheets, wearing those Italian leather shoes.” He leaned down to whisper in Jeff’s ear, his Southern accent dragging every word. “I need to be a bad man for you, Mr. Winger. And you won’t admit it, but you like me bad... That's why we keep seeing each other, and why we will continue with this...”

Jeff didn’t say anything, and Willy smirked, gripping Jeff’s long thighs and pushing them further apart almost aggressively. Jeff’s hands gripped the ex-con’s broad shoulders, halting Willy before he could lower himself between Jeff’s thighs. Willy looked up questioningly.

“Not today...” The lawyer said. “I need you inside me. Need to feel you in-” Jeff had completely missed it when Willy had lubed up his thick finger. He pressed it lightly inside, relishing the way Jeff fell silent with his mouth parted in a silent moan. His first finger met no resistance as it entered and a second soon joined it, drawing a deep gasp out of Jeff’s mouth.

“Does this feel good, Mr. Winger?” Willy asked. “How dangerous it would be, huh? Imagine if the word got out that the straightest lawyer Greendale’s ever met is being fucked so good by some guy who just got out of jail... Your friends would have a field day.”

Jeff’s hand covered his mouth to stop a sob that he had never heard in his life, as Willy’s fingers curled and brushed right over his prostate.

Without him telling, Willy added the third finger. It was a tight stretch, but Jeff only whined in response while Willy teased him.

“Dude, please, move! I need you- oh, yes! Right there, ah. Oh, God!” Jeff’s body shook as Willy hit the right spot again and again with his man fingers. Jeff could only anticipate his veiny dick and its scary thickness.

His own half hard cock was leaking on his stomach, but was pointedly ignored by Willy. The former prisoner loved it when Jeff came untouched under him. It had always been like that. Just because he was in Willy’s small bed, it wasn’t going to change.

“Be louder, Jeff Winger. I want everyone here to know how you call out my name. I need to show them why I want to keep you. You look so beautiful under me, lawyer boy… I’m jealous that someone else can just as easily see you like this.”

Jeff sobbed like never before. “Willy, please.” His big hands were fisting the sheets. “I need you inside. Please-ah!”

The lawyer stuttered as Willy drew back his fingers suddenly, and pressed the tip of his fat glans to Jeff’s hole.

“Going to make you feel this, Mr. Winger...” Willy grunted, thrusting inside Jeff in one go.

Jeff screamed; the stretch was too much and with just enough lube to make it easy for Willy to slide in. Willy hiked his long legs up and Jeff wordlessly wrapped them around him. Willy pressed himself forward till he could kiss the other man, bending him almost in half. Jeff’s hands tightened around Willy’s neck; eyes immediately drawn to Willy’s hairy arms.

The bearded man’s muscled hips moved, pulling out before thrusting back in. Jeff head fell back with a moan, back arching beautifully to join with Willy’s body.

“Fuck, Winger… you feel so good, professor...” He moaned, lips catching on the juncture of Jeff’s collarbones. He pressed the taller man down, trusting wildly as Jeff’s hands scrambled across his broad back trying to find something to hold on to.

Jeff was whimpering and moaning a continuous chant of Willy’s name, as Willy drove in and out of him in frenzied motions, ripping him in half with that thick rod. He didn’t need to tell Willy what to do; Willy knew it like the back of his hand, his tell-tale signs of orgasm, his whimpers, his weaknesses.

“ _Ah! Oh yes, ah ah ah ah_ -” Jeff cried out the same way all those women that he had fucked during his life had cried for him, pulled Willy in for a hungry kiss. Willy complied, kissing every deep moan that came out of Jeff’s lips and drowning his own groans in Jeff’s.

Willy’s hands grabbed Jeff’s waist in a bruising grip and Jeff knew he’d have to wait for half a week before his skin would return to normal. But he loved it in that moment, and his client-turned-lover didn’t let go.

Willy broke apart only as his own orgasm began approaching, reveling in the sight of a flushed Jeff Winger under him as he started thrusting again at a fast pace. Jeff was crying now; his prostate was so sensitive by then that every brush of Willy’s cock sent him one step closer to the edge. He was clenching down on Willy’s down without noticing it, hands splayed onto the other’s back, nails digging in his skin.

“Yes boy, feel so good-” Willy almost screamed. “I know you’re close Winger, let go, baby. God, you’re so good, tightening all around me so good...”

Jeff’s cries increased in volume and he lost it as Willy’s lips covered his again. He came between the two of them, whimpering between Willy’s kisses and crying as the man continued thrusting like a bull despite his sensitivity. He bit his ex-convict’s lip as he clenched on his cock and Willy’s hips jerked, his cock buried inside him as he came, filling him with his manly essence.

Willy continued thrusting shallowly as Jeff’s hairy hole milked him, moaning in the lawyer’s mouth.

Later, when Jeff awoke, it was to a clean smelling Willy sliding inside the sheets beside him. Sleepily, his hands traced the long cut just below Willy’s bicep. It was new, Jeff knew. He’d never seen it before that night.

“What’s this?” he asked sleepily. His fingers brushed his lover’s arm.

Willy just pulled the taller man onto his chest. He switched off the lamps and encased the room in darkness. “You know I don’t like it when you ask me questions.”

“I’m your lawyer, _and_ former teacher...” Jeff tried arguing with his usual tone.

“Sleep now. You have a flight in the morning.” Willy said. “Your friends must be waiting for you back at Greendale, Mr. Winger.”

Jeff didn’t reply. He knew it was wrong, that fucking the man that had had intentions to kill him in the past was wrong. This wasn’t good for any of them, but it felt good. And like every other time, Jeff brushed aside his morality and snuggled closer to Willy.


End file.
